Electroconductive paper and process of making same

ABSTRACT

A paper having a surface adapted for electrostatic printing and a process for preparing such paper; said paper containing at least one monoquaternary nitrogen compound which serves as the electrostatic electroconductive medium.

,United States Patent Inventors Dilip K. Ray-Chaudhuri Somerset;

Stanley Field, Piscataway; Irving D. Hodgkin, Neshanic Station, all of N .J. 816,777

Apr. 16, 1969 Nov. 9, 1971 National Starch and Chemical Corporation New York, N.Y.

Appl. No. Filed Patented Assignee ELECTROCONDUCTIVE PAPER AND PROCESS OF MAKING SAME [50] Field ofSearch 117/201, 154, 218, 76, 86; 162/138 [56] References Cited UNITED STATES PATENTS 3,264,137 8/1966 Gess 117/201 3,335,100 8/1967 Geyer.... 117/201 X 3,348,970 10/1967 Gess 1 17/201 Primary Examiner-William L. Jarvis AtlorneyTh0mas B. Graham ABSTRACT: A paper having a surface adapted for electrostatic printing and a process for preparing such paper; said paper containing at least one monoquatemary nitrogen compound which serves as the electrostatic electroconductive medium.

BACKGROUND OF THE INVENTION This invention relates to novel, electrically conductive paper which is useful in the electrostatic printing art. it relates more particularly to paper having a coated surface adapted for electrostatic printing and which contains at least one monoquaternary nitrogen compound which serves as the electrostatic electroconductive medium. In a further aspect, the invention relates to the process of making the thus described paper.

In electroconductive printing processes the treated surface of the electroconductive paper is subjected to a modulated voltage in a predetermined pattern. The thus-imparted electrostatic charge produces a latent image in accordance with the intensity of the applied voltage. The latent image is subsequently made visible, ordinarily by the application of a powdered reagent carrying a charge opposite to that of the electrostatic charge on the paper; the latter powder being permanently fused to the paper upon being heated or by other selected means. A particular shortcoming of many conductive media which are presently used to produce electroconductive paper lies in their diminished ability to remain conductive in a dry atmosphere, i.e. at relative humidities ranging below about 50 percent.

Broadly stated, it is a primary object of this invention to provide improved, electrically conductive coated paper which is useful in electrostatic printing processes under all ambient conditions including conditions of low relative humidity.

Another object of this invention is to provide electrically conductive coated paper having a surface resistivity, i.e. the reciprocal of conductivity, of from about 4x10 to 2X10 ohms/cm. at relative humidities ranging from about to 50 percent; the latter resistivity values being required in any paper which is to be successfully used in electroconductive processes.

Other objects and advantages of our invention will be made apparent from the following description.

SUMMARY OF THE INVENTION We have now discovered that when certain monoquatemary nitrogen compounds are coated upon, or otherwise introduced, to a paper substrate so as to provide an electrostatic printing surface, the aforementioned objects are all readily achieved, Furthermore, the use of these specified monoquaternary nitrogen compounds does not, surprisingly, require the coincident use of deliquescent salts, such as lithium or zinc chlorides, as was previously thought to be necessary in order to impart a satisfactory level of conductivity with a given concentration of a quaternary ammonium compound. (See, for example, US. Pat. Nos. 3,264,137 and 3,348,970).

The monoquaternary nitrogen compounds suitable for use in the present invention are those which correspond to the following structural formulas:

wherein R is an alkyl group containing from one to 22 carbon atoms; R is a radical selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl, halo-alkyl, halo-alkenyl, haloand groups wherein It may have a value of from 0 to 19; A is an alkylene radical containing from two to seven carbon atoms; X is an alkyl group containing from five to 15 carbon atoms; and Y is an anion selected from the group consisting of the chlorine, bromine, iodine, methosulfate and ethosulfate anions.

The monoquaternary nitrogen compounds useful in the process of this invention are relatively soluble in water, and generally exhibit indeterminate melting points. These compounds are either available commercially or methods for their preparation may be found in the literature.

Among the monoquaternary nitrogen compounds represented by the foregoing structural formulas are:

Group I. Z-Undecyl-l-methyl-l-hydroxyethyl-1,4,5- dihydroimidazolinium chloride and 2-Heptadecyl-lmethyll -hydroxy-propyl-l ,4,5,6-tetrahydropyrimidinium methosulfate,

Group 2. N-lsopentadecyl-N-trimethyl ammonium chloride and N-lsoundecyl-dihydroxyethyl-methyl ammonium chloride,

Group 3. chloride,

Group 4. N-Dodecyl-methylpyrrolidinium chloride,

Group 5. N-Tetradecyl-methyl piperidinium chloride,

Group 6. 2-Hydroxy-3-dodecyl benzyl trimethyl ammonium chloride,

Group 7. N-Hexadecyl-ethyl morpholinium ethosulfate,

Group 8. l,2-trimethylenel -decyl l ,4,5,6,-

tetrahydropyrimidinium bromide,

Group 9. N-Dodecanamidopropyl-trimethyl ammonium chloride,

Group 10. Dodecyl trimethyl ammonium chloride, Tallow (C, C trimethyl ammonium chloride and Tallow (C -Q.) dimethyl chloro-2-butenyl ammonium chloride.

With respect to the concentration of the monoquaternary nitrogen compound which is required in the resulting electroconductive paper, ordinarily, one or more of these compounds should be applied onto a paper substrate so that the thus treated paper contains the monoquaternary nitrogen compound in a concentration of from about 0.5 to 6 pounds per ream (3,000 sq. ft.). An effective degree of conductivity for most electroconductive purposes is achieved with paper containing from about 2 to 5 pounds of the selected compound per ream. The use of an increased concentration of the monoquaternary nitrogen compound, while producing increased conductivity, will, of course, result in increased production costs.

A variety of procedures may be used to prepare the improved electroconductive paper of this invention. For example, in a preferred embodiment, an aqueous solution of the selected monoquaternary nitrogen compound, or a mixture thereof, is admixed with a conventional polymeric coating N'-Dodecanoyl-N,N-dimethyl piperizinium material, ordinarily in the form of an aqueous dispersion, and the resulting blend is then applied to the paper substrate by coating, dipping, spraying, or any other technique that can be utilized for the application of an aqueous coating system onto a paper substrate. Suitable polymeric coating materials include any aqueous based polymeric material of a type ordinarily used for coating paper stock that is to be employed in electroconductive processes but which are, however, compatible with the selected monoquatemary nitrogen compound. Examples of such polymeric coating materials include: (1) polyvinyl acetate and the random copolyrners of vinyl acetate with one or more monomers selected from the group consisting of: (a) the alkyl esters of acrylic and methacrylic acid, wherein said alkyl group contains from one to about 10 carbon atoms, such, for example, as methyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, and the corresponding methacrylate esters; (b) vinyl and vinylidene halides, such, for example, as vinyl chloride and vinylidene chloride; (c) ethylenically unsaturated monocarboxylic acids, such, for example, as acrylic, itaconic, citraconic, and crotonic acids; (d) nitriles of ethylenically unsaturated monocarboxylic acids, such, for example, as acrylonitrile; (e) ethylenically unsaturated dicarboxylic acids, such, for example, as maleic and fumaric acid; (f) anhydrides of ethylenically unsaturated dicarboxylic acids, such, for example, as maleic anhydride; (g) the C,C alkyl esters of maleic and fumaric acid, such, for example, as methyl hydrogen maleate; and, (h) the dialkyl esters of ethylenically unsaturated dicarboxylic acids, wherein said alkyl group contains from one to about eight carbon atoms, such, for example, as dibutyl maleate; (2) polyvinyl alcohol; (3) amylaceous based materials such as starches; starch derivatives such as esters and ethers of starch; and, starch conversion products such as oxidized starches and dextrins; and (4) cellulose derivatives such as methyl cellulose, ethyl cellulose, hydroxyethyl cellulose and hydroxypropyl cellulose. Mixtures of any two or more of the latter coating materials can also be used if desired.

The compositions may, if desired, contain a variety of optional ingredients in order to modify certain properties of the resulting compositions. Such ingredients include, for example, pigments, defoamers, fillers, and the like.

Ordinarily, the concentration of the monoquatemary nitrogen compound in the coating blend is from about 4 to 40 percent, by weight, of the resulting blend. The proportion of polymeric coating material solids in the blend may ordinarily vary from about 5 to 50 percent, by weight, of the resulting blend. The total solids content of the blend should be in the range of from about to 70 percent, by weight.

After coating the paper substrate with the above described coating blend, the paper is ordinarily dried by means of any convenient procedure such, for example, as by passing over a drying roll or by the use of an oven. The properties of the resulting coated paper can be modified, as desired, by varying the concentration and/or the particular type of polymeric coating material which is utilized,

The electroconductive paper of this invention may also be prepared by means of a procedure wherein an aqueous solution of the monoquatemary nitrogen compound is applied to the paper substrate by coating, dipping, spraying, or any other selected means. The concentration of the monoquatemary nitrogen compound which is present in the aqueous solution is not critical and may be varied, as desired, provided that the latter compound is present in the resulting electroconductive paper in a concentration of from about 0.5 to 6 pounds per ream. After being dried, the paper prepared in this manner may subsequently receive an additional coating or sizing of a polymeric material of the type described hereinabove.

In another variation of the process of this invention, an aqueous solution of the selected monoquatemary nitrogen compound can be applied to paper which has previously been coated with a polymeric coating material. Thus, in this procedure, the polymeric coating material, selected from the polymeric coating materials described hereinabove, is applied to the paper whereupon it is dried and the conducting coating is subsequently applied to the surface of the substrate which has received the polymeric coating,

In still another variation of the process of this invention, those paper substrates having a dense, so-called tight surface may be coated with an aqueous solution of the monoquatemary nitrogen compound without the subsequent application, thereto, of a polymeric top coat. For example, an aqueous solution of a monoquatemary nitrogen compound need merely be applied onto the surface of such a substrate whereupon, after being dried, it is ready for use.

It is to be noted that any type of paper stock may be utilized as the substrate material for the novel electroconductive papers of this invention. Further, if desired, the electroconductive paper resulting from any of the above described procedures may be further processed, as for example, by calendering, or other conventional processing steps commonly used in the trade.

This invention will be more fully described in conjunction with the following illustrative examples in which all parts given are by weight unless otherwise noted.

EXAMPLE I This example illustrates the preparation of electroconductive paper typical of this invention by means of a procedure wherein the monoquatemary nitrogen compound is first blended with an aqueous emulsion of a polymeric coating material before its application to the paper substrate.

Two formulations were prepared containing the following components:

Formulation l 154 parts of an aqueous emulsion of polyvinyl acetate having a resin solids content of 55 percent, by weight,

43 parts of an aqueous solution containing 35 percent, by weight of tetramethyl ammonium chloride,

103 parts of water.

Formulation 2 136 parts of an aqueous emulsion of polyvinyl acetate having a resin solids content of 55 percent, by weight, 72 parts of an aqueous solution containing 35 percent, by weight, of tetramethyl ammonium chloride,

92 parts of water.

In each formulation, the aqueous solution of the tetramethyl ammonium chloride compound was diluted with the additional water and the mixture was then slowly stirred into the polyvinyl acetate emulsion.

Each of the above described formulations was applied, by means of a Meyer Wire-Wound Bar, to the sized surface of bleached sulfite paper having a basis weight of 51 pounds per ream. After the coating operation was completed, the paper was air dried for about 1 hour and then placed in an oven set at C. for about 1 minute. The resulting dried coating contained the monoquatemary nitrogen compound in a concentration of about 3 pounds per ream.

Samples of the thus prepared electroconductive paper, each measuring about 2.5 3.0 inches, were cut and conditioned for about 24 hours at relative humidities of 25 and 50 percent at 72 F. The surface resistivity of each sample was determined at the specified humidity by measuring the resistance across two electrodes, spaced 0.75 inches apart on the surface of the paper, using a solid state electrometer.

Table I summarizes the results of the evaluation procedures.

TABLE 1 Percent Surface relative resistivity, Sample humidity ohms/cm.

Paper coated with- Formulation l 60 7. 5X10 Formulation 1. 25 2 6X10 Formulation 2 50 5 6X10" Formulation 2. 25 1 1X10 The above data thus reveal that all of the samples had a EXAMPLE II This example illustrates the preparation of electroconductive paper typical of this invention by means of a procedure wherein the monoquaternary nitrogen compound is applied to the paper in the form of an aqueous solution.

Part A. An aqueous solution of lauryl trimethyl ammonium chloride having a concentration of 35 percent, by weight, was

onto a surface of bleached southern kraft paper having a basis weight of 48 pounds per ream. After the tubsizing was completed, the paper was dried for 1 hour and then placed in an oven set at 100 C. for about 1 minute. The resulting dried paper thus contained the lauryl trimethyl ammonium chloride in a concentration of 2.41 pounds per ream.

Part B. In a variation of the above procedure, the aqueous solution of lauryl trimethyl ammonium chloride was applied to l the paper stock as used in Part A by means of a Meyer Wire- Wound Bar. The coating equipment was adjusted to provide a final dry coating of 3.57 pounds of the lauryl trimethyl ammonium chloride per ream.

Measurements of the surface resistivity of samples of each of the thus prepared electroconductive papers were then made at 72 F. and at relative humidities of 50, 35 and percent, respectively. Table ll summarizes the results of these determinations.

The above data thus reveal that all of the samples had a printing surface suitable for electroconductive printing regardless of the low relative humidity at which they had been conditioned.

EXAMPLE III This example illustrates the preparation of a typical coating blend containing tetramethyl ammonium chloride as the electroconductive compound along with a combination of polyvinyl acetate and a chemically derivatized starch which served as the polymeric coating component. Clay is included in the blend in order to improve the opacity of the resulting coating as well as to serve as an extender.

An aqueous emulsion of polyvinyl acetate having a resin solids content of 55 percent, by weight. 54.4 parts A suspension of a low viscosity cationic corn starch which was prepared by treating corn starch with b-diethyl amino ethyl chloride hydrochloride according to the procedure described in US. Pat. No. 2,813,093 The suspension, which contained 15 percent, by weight, of the cationic starch, had been precooked for a period of 15 minutes at about 200 F. 200.0 parts Clay 20.0 parts An aqueous solution containing tetramethyl ammonium chloride Water 1000 parts The blend was prepared by admixing the clay with the precooked starch suspension. Thereafter, the polyvinyl acetate emulsion, the aqueous solution of tetramethyl am- 35 percent, by weight, of

52.! parts monium chloride, and water were each in turn admixed with the clay-starch suspension, and the resulting blend was stirred until a homogeneous composition was obtained.

This composition was applied, by means of an air knife coater, onto bleached sulfite paper having a basis weight of 51 pounds per ream so as to yield an electroconductive paper which, after drying, contained about 3.6 pounds of tetramethyl ammonium chloride per ream. The thus prepared paper exhibited surface resistivity values which were comparable to those of the electroconductive papers whose preparation was described in Examples l and II.

EXAMPLE IV This example illustrates the preparation and use of four coating formulations comprising blends containing varying proportions of a number of different monoquaternary nitrogen compounds and polymeric coating materials.

Subsequent to their preparation which was accomplished by means of the procedure described in example i, each of the formulations described below was coated, by means of an air knife coater, onto bleached sulfite paper having a basis weight of 5 1 pounds per ream so as to yield a coating which, after drying, contained from about 3 to 5 pounds per ream of the selected monoquaternary compound.

Formulation 1 An aqueous emulsion of polyvinyl acetate having a resin solids content of 55 percent, by weight. 100 parts An aqueous solution containing 35 percent, by weight, of

dodecyl trimethyl ammonium chloride. 40 parts Water parts.

Formulation 2 An aqueous emulsion of polyvinyl acetate having a resin solids content of 55 percent, by weight. parts A suspension of a low viscosity, acetylated starch containing 15 percent solids, by weight. The suspension had been precooked for a period of about 15 minutes at about 200 F. 248 parts An aqueous solution containing 35 percent, by weight, of tetradecyl trimethyl ammonium chloride. 66 parts. Formulation 3 An aqueous emulsion of polyvinyl acetate having a resin solids content of 55 percent, by weight. 100 parts An aqueous solution containing 20 percent, by weight, of

polyvinyl alcohol 8 parts An aqueous solution containing 35 percent, by weight, of N- methyl, N-decyl pyrrolidinium bromide 70 parts. Formulation 4 An aqueous solution containing 20 percent, by weight, of

polyvinyl alcohol 100 parts An aqueous solution containing 35 percent, by weight, of N hexadecyl-ethyl morpholinium ethosulfate 24 parts.

Each of the resulting electroconductive papers which had been prepared with the above described coating formulations exhibited surface resistivity values which were comparable to those of the electroconductive papers whose preparation was described in example I and ll.

EXAMPLE V This example illustrates the excellent conductivity achieved with a number of representative monoquaternary nitrogen compounds when used for the preparation of electroconductive papers according to the process of this invention.

Aqueous solutions of each of the compounds listed in table II], hereinbelow, were coated onto sized paper by means of a Meyer Wire-Wound Bar. On completion of the coating procedure, the various samples were air dried and then dried in an oven set at 100 C. for about 1 minute. in each case, the selected monoquaternary nitrogen compound was present in the resulting electroconductive papers in a concentration ranging from about 2 to 4 pounds per ream.

TABLE III Surface resistivity,

Coating ohms/cm. at percent by weight, relative humidity pounds/ 2. O8 7. 9x10 7. 4X10 The above data clearly demonstrate that all of the samples had a printing surface suitable for electroconductive printing regardless of the low relative humidity at which they were conditioned.

What is claimed is:

l. A paper having a printing surface adapted for electroconductive printing, said paper containing at least one monoquaternary nitrogen compound selected from the group wherein R is an alkyl group containing from one to 22 carbon atoms; R is selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl, halo-alkyl, halo-alkenyl, halo-aralkyl,

HOCH CHOHCH HOCH CH- ),,-OCH CH an R Compound ream 35% 25% 1. Stearamidopropyl tri- H- O IIJHCHQ) O CHCHr- CH2 u H:

wherein n may have a value of from 0 to 19; A is an alkylene radical containing from two to seven carbon atoms; X is an group consisting of the chlorine, bromine, iodine, methosulfate and ethosulfate anions.

2. The

paper. 3. The paper of claim 1, wherein said monoquaternary nitrogen compound is selected from the group consisting of:

2-undecyl- 1 -methyll-hydroxyethyll ,4,5-

dihydroimidazolinium chloride; Z-heptadecyl- 1 -methyl- 1 -hydroxypropyll ,4,5 ,6-

tetrahydropyrimidinium methosulfate; N-isopentadecyl-N-trimethyl ammonium chloride; N-isoundecyl-dihydroxyethyl-methyl ammonium chloride; N '-dodecanoyl-N,N-dimethyl piperizinium chloride; N-dodecyl-methylpyrrolidinium chloride; N-tetradecyl-methyl piperidinium chloride; 2-hydroxy-3-dodecyl benzyl trimethyl ammonium chloride; N-hexadecyl-ethyl morpholinium ethosulfate; l,2-trimethylenel -decyll ,4.5,o-tetrahydropyrimidinium bromide; N-dodecanamidopropyl-trimethyl ammonium dodecyl trimethyl ammonium chloride; tallow(C, C, trimethyl ammonium chloride; tallow(C, C|a) dimethyl chloro-Z-butenyl chloride; tetramethyl ammonium chloride; lauryl trimethyl ammonium chloride; tetradecyl trimethyl ammonium chloride;

-methyl, N-decyl pyrrolidinium bromide; stearamidopropyl trimethyl ammonium chloride; N-cetyl, N-ethyl morpholinium ethosulfate; N-octadecylphenylmethyl, dimethyl ammonium chloride; l,2-dimethyll -decyl-l .4,5,6-tetrahydropyrimidinium bromide; and

N-cyclohexyl trimethyl ammonium chloride. 4. The paper of claim 1 coated chloride;

ammonium monoquaternary nitrogen compound selected from the groups having the general formulas:

A R (3H3 /R N Y; IlIC-N \R Y- N =CR C H3 X 0 H3 O R, R Ram g [F g/ CH3 R,

R R N/ 1Y7 Y- \R R CH;I' I\ R t R 0 l J Y"; 11-1 1 p/ l Y- R l /N 9 l 0 H N-isoundecyl-dihydroxyethyl-mcthyl ammonium chloride; 1 and 4 I N '-dodecanoyl-N,N-dimethyl piperizinium chloride;

\ N-dodecyl-methyl p rrolidinium chloride;

N-tetradecybmethyfpiperidinium chloride; 9 10 2-hydroxy-3-dodecyl benzyl trimethyl ammonium chloride; N-hexadecyl-ethyl morpholinium ethosulfate; wherein R is an alkyl group containing from one to 22 carbon 1 2-tri th -].d 4 5fiq t h d ri idi i atoms; R is selected from the group consisting of alkyl, aryl, bromide; ky y l yl. hal -alkyl. h l lkeny N-dodecanamidopropyl-trimethyl ammonium chloride;

dodec ltrimethyl ammonium chloride; HOCH2CHOHCH H OCHCH2 )rOCHCHZ" and tallowz C C trimethyl ammonium chloride;

tallow (C -C dimethyl chloro-2-butenyl ammonium H 0 CHCHz) 0 OHCH,- chloride;

\ CH2 Ha tetramethyl ammonium chloride;

l5 lauryl trimethyl ammonium chloride; wherein n may have a value of from 0 to 19; A 18 an alkylene tetmdecyl "methyl ammonium chloride;

radical containing from two to seven carbon atoms; X is an N meth yl, N-decyl pyrrolidimum bromide, alkyl group containing from five to carbon atoms; and Y IS steatamidopmpyl trimethyl ammonium chloride; an anion selected from the group consisting of the chlorine, any], Methyl morphofinium ethosulfate;

bromine iodine methmqlfate and f f anions 20 N-octadccylphenylmcthyl, dimethyl ammonium chloride; T Pmess clam? 5 F" 1,2-dimethyl-l-decyl-l ,4,5,6-tetrahydropyrimidinium bronitrogen compound 1s applied in a concentration ranging from mide. and

about to Pounds Q ream ofszfld e N-cyclohexyl trimethyl ammonium chloride. 7. The process of claim 5, wherein said monoquate 8. The process of claim 5, wherein said printing surface is Imogen compound selected from the group cons'st'ng of: coated with at least one coating material selected from the 'f j f x Y group consisting of: (l) polyvinyl acetate and the random dlhydrolmldazohmum chlonde; copolymers of vinyl acetate; (2) polyvinyl alcohol; (3)

'm f' amylaceous based materials; and (4) cellulose derivatives.

tetrahydropynmidmium methosulfate; It I It N-isopentadecyl-N-trimethyl ammonium chloride; 

2. The paper of claim 1, wherein said monoquaternary nitrogen compound is present in a concentration ranging from about 0.5 to 6.0 pounds per ream of said paper.
 3. The paper of claim 1, wherein said monoquaternary nitrogen compound is selected from the group consisting of; 2-undecyl-1-methyl-1-hydroxyethyl-1,4,5-dihydroimidazolinium chloride; 2-heptadecyl-1-methyl-1-hydroxypropyl-1,4,5,6-tetrahydropyrimidinium methosulfate; N-isopentadecyl-N-trimethyl ammonium chloride; N-isoundecyl-dihydroxyethyl-methyl ammonium chloride; N''-dodecanoyl-N,N-dimethyl piperizinium chloride; N-dodecyl-methylpyrrolidinium chloride; N-tetradecyl-methyl piperidinium chloride; 2-hydroxy-3-dodecyl benzyl trimethyl ammonium chloride; N-hexadecyl-ethyl morpholinium ethosulfate; 1,2-trimethylene-1-decyl-1,4,5,6-tetrahydropyrimidinium bromide; N-dodecanamidopropyl-trimethyl ammonium chloride; dodecyl trimethyl ammonium chloride; tallow(C14-C18) trimethyl ammonium chloride; tallow(C14-C18) dimethyl chloro-2-butenyl ammonium chloride; tetramethyl ammonium chloride; lauryl trimethyl ammonium chloride; tetradecyl trimethyl ammonium chloride; N-methyl, N-decyl pyrrolidinium bromide; stearamidopropyl trimethyl ammonium chloride; N-cetyl, N-ethyl morpholinium ethosulfate; N-octadecylphenylmethyl, dimethyl ammonium chloride; 1,2-dimethyl-1-decyl-1,4,5,6-tetrahydropyrimidinium bromide; and N-cyclohexyl trimethyl ammonium chloride.
 4. The paper of claim 1, wherein said printing surface is coated with at least one coating material selected from the group consisting of: (1) polyvinyl acetate and the random copolymers of vinyl acetate; (2) polyvinyl alcohol; (3) amylaceous based materials; and (4) cellulose derivatives.
 5. A process of manufacturing electroconductive paper having a printing surface adapted for electroconductive printing, said process comprising applying to paper at least one monoquaternary nitrogen compound selected from the groups having the general formulae:
 6. The process of claim 5 wherein said monoquaternary nitrogen compound is applied in a concentration ranging from about 0.5 to 6.0 pounds per ream of said paper.
 7. The process of claim 5, wherein said monoquaternary nitrogen compound is selected from the group consisting of: 2-undecyl-1-methyl-1-hydroxyethyl-1,4,5-dihydroimidazolinium chloride; 2-heptadecyl-1-methyl-1-hydroxypropyl-1,4,5,6-tetrahydropyrimidinium methosulfate; N-isopentadecyl-N-trimethyl ammonium chloride; N-isoundecyl-dihydroxyethyl-methyl ammonium chloride; N''-dodecanoyl-N,N-dimethyl piperizinium chloride; N-dodecyl-methyl pyrrolidinium chloride; N-tetradecyl-methyl piperidinium chloride; 2-hydroxy-3-dodecyl benzyl trimethyl ammonium chloride; N-hexadecyl-ethyl morpholinium ethosulfate; 1,2-trimethylene-1-decyl-1,4,5,6-tetrahydropyrimidinium bromide; N-dodecanamidopropyl-trimethyl ammonium chloride; dodecyl trimethyl ammonium chloride; tallow(C14-C18) trimethyl ammonium chloride; tallow (C14-C18) dimethyl chloro-2-butenyl ammonium chloride; tetramethyl ammonium chloride; lauryl trimethyl ammonium chloride; tetradecyl trimethyl ammonium chloride; N-methyl, N-decyl pyrrolidinium bromide; stearamidopropyl trimethyl ammonium chloride; N-cetyl, N-ethyl morpholinium ethosulfate; N-octadecylphenylmethyl, dimethyl ammonium chloride; 1,2-dimethyl-1-decyl-1,4,5,6-tetrahydropyrimidinium bromide; and N-cyclohexyl trimethyl ammonium chloride.
 8. The process of claim 5, wherein said printing surface is coated with at least one coating material selected from the group consisting of: (1) polyvinyl acetate and the random copolymers of vinyl acetate; (2) polyvinyl alcohol; (3) amylaceous based materials; and (4) cellulose derivatives. 